CN109400736A - The synthetic method of double esterification 3,4,5-trihydroxy benzoic acid base bagasse xylan benzoic ether - Google Patents
The synthetic method of double esterification 3,4,5-trihydroxy benzoic acid base bagasse xylan benzoic ether Download PDFInfo
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- C08B37/0057—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Xylans, i.e. xylosaccharide, e.g. arabinoxylan, arabinofuronan, pentosans; (beta-1,3)(beta-1,4)-D-Xylans, e.g. rhodymenans; Hemicellulose; Derivatives thereof
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Abstract
The invention discloses a kind of synthetic methods of double esterification 3,4,5-trihydroxy benzoic acid base bagasse xylan benzoic ether.3 generated with Gallic Acid through acetylation, acyl chloride reaction; 4,5- triacetyl chlorobenzoyl chlorides are esterifying agent, in N; dinethylformamide) esterification is carried out with bagasse xylan in solvent synthesizes bagasse xylan Gallic Acid ester；Then using benzoic acid as esterifying agent, triethylamine is that catalyst carries out second step esterification, and double esterification Gallic Acid base bagasse xylan benzoate derivatives are synthesized in dichloromethane solvent.The present invention is based on the unique bioactivity of xylan esterification derivative, and by introducing two kinds of active groups, products therefrom not only increases the bioactivity of xylan, while also having widened xylan derivative in the application range in the fields such as medicine, biology, functional material.
Description
Technical field
The present invention relates to field of fine chemical, provide a kind of double esterification Gallic Acid base bagasse xylan benzene
The synthetic method of formic acid esters.
Background technique
Bagasse is the industrial residues of Guangxi sugaring industry, wherein the xylan being rich in can pass through physics and chemical modification
It has been converted into high value-added product.The mono-esterification modification of xylan is one of common method of modifying of xylan, and xylan is logical
Its product not only all increases and improves in structure and thermal stability etc. after over-churning, also enhances anti-oxidant, AntiHIV1 RT activity, resists
The bioactivity such as tumour, antiviral.
Stronger gallic acid, that is, the Gallic Acid of bioactivity is esterified with bagasse xylan, it can be with
Enhance the HIV-resistant activity of xylan.Since the mono-esterification of xylan only introduces a kind of bio-active group, general degree of substitution also compared with
Low, the AntiHIV1 RT activity effect of generation is undesirable.For the bioactivity for further increasing bagasse xylan, draw on bagasse xylan chain
Enter second of active group and double esterification reaction is carried out to bagasse xylan, its derivative is made to introduce two kinds of bio-active groups, it can
The bioactivity such as the AntiHIV1 RT activity of bagasse xylan derivative are improved by a relatively large margin.
The 3,4,5- triacetyl that the present invention is generated with 3,4,5-trihydroxy benzoic acid through acetylation, acyl chloride reaction first
Chlorobenzoyl chloride is esterifying agent, carries out esterification with bagasse xylan in n,N-Dimethylformamide (DMA) solvent and synthesizes sugarcane
Slag xylan 3,4,5-trihydroxy benzoic acid ester；Then using benzoic acid as esterifying agent, triethylamine is that catalyst carries out second step ester
Change reaction, it is derivative that double esterification Gallic Acid base bagasse xylan benzoic ether is synthesized in dichloromethane solvent
Object.Product not only increases the bioactivity of xylan, while also having widened xylan derivative in medicine, biology, function material
The application range in the fields such as material.
Summary of the invention
The present invention be in order to overcome bagasse xylan mono-esterification in terms of AntiHIV1 RT activity limitation, realize bagasse xylan tool
There are two types of different groups to generate HIV-resistant activity, so providing a kind of double esterification Gallic Acid base bagasse wood
The synthetic method of glycan benzoic ether.
Specific steps of the invention are as follows:
(1) 5~10g bagasse xylan is obtained into butt sugarcane to constant weight in drying 24 hours in 60 DEG C of vacuum constant temperature drying boxes
Slag xylan.
(2) by 6~10g3,4,5- trihydroxybenzoic acids are added in the four-hole boiling flask of 250mL, and it is added 15 thereto~
22mL analyzes pure acetic anhydride and 11~16mL analyzes pure pyridine, and control ice bath temperature is 5~15 DEG C, and it is small to stir lower reaction 5~6
When.Be added 30~40mL mass fraction be 20%~30% hydrochloric acid solution, stir evenly 3,4,5- triacetyl benzoic acid are thick
Product.
(3) 3,4,5- triacetyl benzoic acid crude product obtained by step (2) is filtered, and is sufficiently washed with 10~15mL distilled water
It is filtered after precipitating 3 times, filter cake send into 50 DEG C of vacuum constant temperature drying boxes dry 24 hours to constant weight, obtains 3,4,5- triacetyl benzene first
Acid.
(4) 3,4,5- triacetyl benzoic acid obtained by 5~10g step (3) is taken to be added in 250mL four-hole boiling flask, and to its
30~45mL of middle addition analyzes pure hexamethylene and 1~2mL analyzes pure N, and N '-dimethyl formamide, after mixing evenly, system heat up
To 60~80 DEG C, stirs the lower 15~45mL that is added dropwise and analyze pure thionyl chloride, control is added dropwise in 20~30 minutes, continues to stir
Mix reaction 2~4 hours.
(5) reaction solution obtained by step (4) is poured into Rotary Evaporators, it is concentrated by evaporation 20 under conditions of 60~80 DEG C~
60 minutes, obtain the solid of rufous.It places it in drying 24 hours in 50 DEG C of vacuum constant temperature drying boxes and obtains 3,4,5- tri- to constant weight
Acetyl chlorobenzoyl chloride.
(6) butt bagasse xylan obtained by 2~5g step (1) is weighed in 250mL four-hole boiling flask, then it is added 10~
20mL analyzes pure N,N-dimethylformamide, 1~4.5g dehydrating agent N, N- dicyclohexylcarbodiimide and 0.2~0.6g catalyst
Ammonium persulfate stirs 25 minutes.
(7) 3,4,5- triacetyl chlorobenzoyl chloride obtained by 1.5~6.0g step (5) is weighed in 100mL beaker, addition 20~
35mL n,N-Dimethylformamide is heated to 35~40 DEG C in water-bath, and stirring and dissolving obtains triacetyl nutgall acyl solutions of chlorine.It sets
It is spare in 100mL constant pressure funnel.
(8) step (7) acquired solution is slowly added into system obtained by step (6)；It flows back under the conditions of 60 DEG C, continuously
Reaction 4 hours.
(9) step (8) resulting material is filtered, and respectively successively with the analysis of 15~25mL analysis pure acetone, 20~25mL
Pure dehydrated alcohol is respectively washed, is filtered 3 times, obtains filter cake.Filter cake is put into surface plate, is placed in 50 DEG C of vacuum constant temperature drying boxes dry
24 hours to constant weight to get triacetyl bagasse xylan gallate.
(10) triacetyl bagasse xylan gallate obtained by 3~8g step (9) is weighed in 30~50mL sodium bicarbonate
Dehydrated alcohol saturated solution in；It is stirred at room temperature 20~30 minutes, until pH of suspension is no longer changed.
(11) suspension obtained by step (10) is filtered, filter cake is distilled water washing 3 times with 10~15mL, is placed in 50 DEG C of vacuum
24 hours are dried in thermostatic drying chamber to constant weight to get Gallic Acid base bagasse wood polyester.
It (12) is that 3%~5% sodium hydroxide solution is added sequentially to by 0.5~1g benzoic acid, 20~30mL mass fraction
In the four-hole boiling flask of 250mL, reaction is stirred at room temperature 0.5~1 hour, obtains sodium benzoate salting liquid.
(13) it weighs 3,4,5-trihydroxy benzoic acid base bagasse xylan ester obtained by 1~5g step (11) and is added to step
(12) it in gained sodium benzoate salting liquid, stirs 2~4 hours at room temperature.It is 1%~5% that 10~15mL mass fraction, which is added,
Hydrochloric acid adjusts reaction solution pH to 6~7, adds 0.5~1.0mL and analyzes pure triethylamine, is warming up to 30~45 DEG C, stirs lower reaction
3~7 hours.The hydrochloric acid tune pH to 4~5 for being after reaction 5% with 10~15mL mass fraction, is cooled to 20~30 DEG C, after
Continuous reaction 1 hour.
(14) 20~30mL dehydrated alcohol is added in reaction solution obtained by step (13), stirring filters after precipitating is precipitated, and filters
Cake 15~20mL deionized water and 5~10mL dehydrated alcohol are washed, are filtered 2~3 times.Gained filter cake is put into surface plate,
Dry 24 hours are placed in 50 DEG C of vacuum constant temperature drying boxes to get target product double esterification Gallic Acid base bagasse
Xylan benzoic ether.
(15) carboxylic esterification degree of substitution, operating method are carried out with determination of acid-basetitration bagasse xylan double esterification derivative
As follows: the Product samples of precise about 0.5g are put into 250mL conical flask, and 5mL deionized water is added, and then instill 3 drop phenol
Phthalein indicator.The sodium hydroxide solution of 2.5mL concentration 0.5mol/L is added, shakes up.Concussion saponification 1 hour at room temperature.With
10mL deionized water rinses the inner wall of plug and conical flask, then be titrated to 0.5mol/L hydrochloric acid standard solution it is colourless, as eventually
Point.The volume V of record consumption hydrochloric acid standard solution1.Under the same conditions, blank drop is carried out with the bagasse xylan before esterification
It is fixed, record consumption hydrochloric acid standard solution volume V0.The calculation formula of carboxylic esterification degree of substitution (DS) is as follows:
In formula:
Wc--- contain the mass fraction of ester carbonyl group, % in double esterification bagasse xylan；
V0--- titration bagasse xylan uses HCI standard solution volume, mL；
V1--- HCl standard solution volume used in titration target product, mL；
CHCl--- the concentration of HCl, mol/L；
The quality of m --- sample, g；
M --- the relative molecular mass of acyl group dehydration xylose units；
132 --- the relative molecular mass of bagasse xylan dewatering unit；
DS --- ester carbonyl group degree of substitution.
The present invention is by carrying out secondary esterification with para Toluic Acid and drawing on the basis of synthesizing bagasse xylan gallate
Enter another group synthesis 3,4,5-trihydroxy benzoic acid base bagasse xylan benzoic ether double esterification with HIV-resistant activity to spread out
Biology.Synthetic technological condition is easily-controllable, and product is not only mentioned in terms of the application performances such as bioactivity, water solubility, surface-active
Height, and also there is certain potential using value in fields such as medicine, materials.
Detailed description of the invention
Fig. 1 is the SEM photograph of bagasse xylan.
Fig. 2 is the SEM photograph of double esterification 3,4,5-trihydroxy benzoic acid base bagasse xylan benzoic ether.
Fig. 3 is original bagasse xylan IR figure.
Fig. 4 is that the IR of double esterification 3,4,5-trihydroxy benzoic acid base bagasse xylan benzoic ether schemes.
Fig. 5 is the XRD diagram of former bagasse xylan.
Fig. 6 is the XRD diagram of double esterification 3,4,5-trihydroxy benzoic acid base bagasse xylan benzoic ether.
Fig. 7 is TG the and DTG curve of former bagasse xylan.
Fig. 8 is TG the and DTG curve of double esterification 3,4,5-trihydroxy benzoic acid base bagasse xylan benzoic ether.
Specific embodiment
Embodiment:
(1) 6g bagasse xylan is obtained into butt bagasse wood to constant weight in drying 24 hours in 60 DEG C of vacuum constant temperature drying boxes
Glycan.
(2) 8g Gallic Acid is added in the four-hole boiling flask of 250mL, and 18mL analysis is added thereto
Pure acetic anhydride and 15mL analyze pure pyridine, and control ice bath temperature is 5 DEG C, stir lower reaction 6 hours.30mL mass fraction, which is added, is
25% hydrochloric acid solution stirs evenly 3,4,5- triacetyl benzoic acid crude products.
(3) 3,4,5- triacetyl benzoic acid crude product obtained by step (2) is filtered, and sufficiently washs precipitating with 15mL distilled water
It is filtered after 3 times, filter cake send into 50 DEG C of vacuum constant temperature drying boxes dry 24 hours to constant weight, obtains 3,4,5- triacetyl benzoic acid.
(4) 3,4,5- triacetyl benzoic acid obtained by 6g step (3) is taken to be added in the four-hole boiling flask of 250mL, and thereto
35mL is added and analyzes pure hexamethylene and the pure N of 1mL analysis, N '-dimethyl formamide, after mixing evenly, system are warming up to 70 DEG C, stir
It mixes lower dropwise addition 25mL and analyzes pure thionyl chloride, control is added dropwise in 25 minutes, continues to be stirred to react 3 hours.
(5) reaction solution obtained by step (4) is poured into Rotary Evaporators, is concentrated by evaporation 30 minutes under conditions of 65 DEG C,
Obtain the solid of rufous.It places it in drying 24 hours in 50 DEG C of vacuum constant temperature drying boxes and obtains 3,4,5- triacetyl benzene to constant weight
Formyl chloride.
(6) butt bagasse xylan obtained by 3g step (1) is weighed in 250mL four-hole boiling flask, and 12mL analysis is then added
Pure n,N-Dimethylformamide, 2g dehydrating agent N, N- dicyclohexylcarbodiimide and 0.4g catalyst ammonium persulfate stir 25 points
Clock.
(7) 3,4,5- triacetyl chlorobenzoyl chloride obtained by 4g step (5) is weighed in 100mL beaker, and 25mL N, N- bis- is added
Methylformamide is heated to 35 DEG C in water-bath, and stirring and dissolving obtains triacetyl nutgall acyl solutions of chlorine.It is placed in 100mL constant pressure addition
It is spare in funnel.
(8) step (7) acquired solution is slowly added into system obtained by step (6)；It flows back under the conditions of 60 DEG C, continuously
Reaction 4 hours.
(9) step (8) resulting material is filtered, and respectively successively with the pure anhydrous second of analysis of 20mL analysis pure acetone, 25mL
Alcohol is respectively washed, is filtered 3 times, obtains filter cake.
(10) filter cake obtained by step (9) is placed in 50 DEG C of vacuum constant temperature drying boxes dry 24 hours to constant weight to get three
Acetyl bagasse xylan gallate.
(11) triacetyl bagasse xylan gallate obtained by 6g step (10) is weighed in the anhydrous of 40mL sodium bicarbonate
In alcohol saturated solution；Gained is stirred at room temperature, until pH of suspension is no longer changed.
(12) suspension obtained by step (11) is filtered, filter cake is distilled water washing 3 times with 15mL, is placed in 50 DEG C of vacuum constant temperatures
24 hours are dried in drying box to constant weight, i.e. Gallic Acid base bagasse wood polyester.
(13) 0.7g benzoic acid, the sodium hydroxide solution that 20mL mass fraction is 3% are added sequentially to four mouthfuls of 250mL
In flask, is reacted 1 hour in 10 DEG C of at a temperature of magnetic agitation, sodium benzoate salting liquid is made.
(14) it weighs 3,4,5-trihydroxy benzoic acid base bagasse xylan ester obtained by 2g step (12) and is added to step (13)
In gained sodium benzoate salting liquid, stir 3 hours at room temperature.The hydrochloric acid that 15mL mass fraction is 3% is added and adjusts reaction solution pH
To 6, adds 1.0mL and analyze pure triethylamine, be warming up to 35 DEG C, stir lower reaction 5 hours.After reaction with 15mL mass point
The hydrochloric acid tune pH to 4 that number is 5%, is cooled to 25 DEG C, the reaction was continued 1 hour.
(15) reaction solution obtained by step (14) is poured into 100mL beaker, the dehydrated alcohol of 30mL is then added thereto,
Precipitating is precipitated to filter, gained filter cake 15mL deionized water will be filtered and 10mL dehydrated alcohol is successively washed and filtered, repeat 3
It is secondary.Gained filter cake is placed in in 50 DEG C of vacuum constant temperature drying box dry 24 hours to get target product double esterification 3,4,5- tri-
Hydroxybenzoic acid base bagasse xylan benzoic ether.
(14) using acid-base titration to the ester of double esterification 3,4,5-trihydroxy benzoic acid base bagasse xylan benzoic ether
Change degree is measured, and measures DS=0.37.
Product is analyzed through IR, in 1731.25cm-1And 1249.56cm-1There are two new characteristic absorption peaks in place, respectively
Corresponding is ester carbonyl group and phenolic hydroxyl group；1510.55cm-1It is the infrared signature absorption peak of phenyl ring.XRD analysis map, which can be seen that, to spread out
The height at peak increasing and get higher with measured matter crystalline content is penetrated, the width of crystal region is also broadened；Peak value is higher,
It is thinner, illustrate that the crystallinity of the double esterification derivative is higher, crystal region is bigger.By the external shape for observing the SEM figure of product
Looks, it is known that by the modified target product generated of double esterification, the gap between particle significantly reduces, while surface and xylan
Compared to more rougher.It is analyzed through TG-DTG, the thermogravimetric decomposable process and bagasse xylan of double esterification product are roughly the same, illustrate double
The thermal stability variation of esterification derivative is little.
Claims (1)
1. a kind of synthetic method of double esterification Gallic Acid base bagasse xylan benzoic ether, it is characterised in that tool
Body step are as follows:
(1) 5 ~ 10g bagasse xylan it is poly- to be obtained into butt bagasse wood to constant weight in drying 24 hours in 60 DEG C of vacuum constant temperature drying boxes
Sugar；
(2) by 6 ~ 10g3,4,5- trihydroxybenzoic acids are added in the four-hole boiling flask of 250mL, and 15 ~ 22mL points are added thereto
Pure acetic anhydride and 11 ~ 16mL analysis pure pyridine are analysed, control ice bath temperature is 5 ~ 15 DEG C, is stirred lower reaction 5 ~ 6 hours；Addition 30 ~
The hydrochloric acid solution that 40mL mass fraction is 20% ~ 30%, stirs evenly to obtain 3,4,5- triacetyl benzoic acid crude products；
(3) 3,4,5- triacetyl benzoic acid crude product obtained by step (2) is filtered, and sufficiently washs precipitating with 10 ~ 15 mL distilled water
It is filtered after 3 times, filter cake send into 50 DEG C of vacuum constant temperature drying boxes dry 24 hours to constant weight, obtains 3,4,5- triacetyl benzoic acid；
(4) it takes 3,4,5- triacetyl benzoic acid obtained by 5 ~ 10g step (3) to be added in 250mL four-hole boiling flask, and is added thereto
30 ~ 45mL analyzes pure hexamethylene and 1 ~ 2mL analyzes pure N, and N '-dimethyl formamide, after mixing evenly, system is warming up to 60 ~ 80
DEG C, it stirs the lower 15 ~ 45mL that is added dropwise and analyzes pure thionyl chloride, control is added dropwise in 20 ~ 30 minutes, continues to be stirred to react 2 ~ 4
Hour；
(5) reaction solution obtained by step (4) is poured into Rotary Evaporators, 20 ~ 60 points is concentrated by evaporation under conditions of 60 ~ 80 DEG C
Clock obtains the solid of rufous；It places it in drying 24 hours in 50 DEG C of vacuum constant temperature drying boxes and obtains 3,4,5- triacetyls to constant weight
Chlorobenzoyl chloride；
(6) butt bagasse xylan obtained by 2 ~ 5 g steps (1) is weighed in 250 mL four-hole boiling flasks, and 10 ~ 20 mL are then added
Analyze pure N,N-dimethylformamide, 1 ~ 4.5 g dehydrating agent N, N- dicyclohexylcarbodiimide and 0.2 ~ 0.6 g catalyst over cure
Sour ammonium stirs 25 minutes；
(7) 3,4,5- triacetyl chlorobenzoyl chloride obtained by 1.5 ~ 6.0g step (5) is weighed in 100 mL beakers, and 20 ~ 35 mL are added
N,N-Dimethylformamide is heated to 35 ~ 40 DEG C in water-bath, and stirring and dissolving obtains triacetyl nutgall acyl solutions of chlorine；It is placed in 100mL
It is spare in constant pressure funnel；
(8) step (7) acquired solution is slowly added into system obtained by step (6)；It flows back under the conditions of 60 DEG C, successive reaction
4 hours；
(9) step (8) resulting material is filtered, and respectively successively with the pure nothing of analysis of 15 ~ 25 mL analysis pure acetone, 20 ~ 25 mL
Water-ethanol is respectively washed, is filtered 3 times, obtains filter cake；Filter cake is put into surface plate, and it is small to be placed in 50 DEG C of vacuum constant temperature drying boxes dry 24
Up to constant weight to get triacetyl bagasse xylan gallate；
(10) triacetyl bagasse xylan gallate obtained by 3 ~ 8 g steps (9) is weighed in the nothing of 30 ~ 50 mL sodium bicarbonates
In water-ethanol saturated solution；It is stirred at room temperature 20 ~ 30 minutes, until pH of suspension is no longer changed；
(11) suspension obtained by step (10) is filtered, filter cake is distilled water washing 3 times with 10 ~ 15mL, is placed in 50 DEG C of vacuum constant temperatures
24 hours are dried in drying box to constant weight to get Gallic Acid base bagasse wood polyester；
It (12) is that 3% ~ 5% sodium hydroxide solution is added sequentially to the four of 250mL by 0.5 ~ 1g benzoic acid, 20 ~ 30mL mass fraction
In mouth flask, reaction is stirred at room temperature 0.5 ~ 1 hour, obtains sodium benzoate salting liquid；
(13) it weighs 3,4,5-trihydroxy benzoic acid base bagasse xylan ester obtained by 1 ~ 5g step (11) and is added to step (12) institute
It obtains in sodium benzoate salting liquid, stirs 2 ~ 4 hours at room temperature；The hydrochloric acid that 10 ~ 15mL mass fraction is 1% ~ 5% is added and adjusts reaction
Liquid pH to 6 ~ 7 adds 0.5 ~ 1.0mL and analyzes pure triethylamine, is warming up to 30 ~ 45 DEG C, stirs lower reaction 3 ~ 7 hours；Reaction knot
The hydrochloric acid tune pH to 4 ~ 5 that Shu Houyong 10 ~ 15mL mass fraction is 5%, is cooled to 20 ~ 30 DEG C, the reaction was continued 1 hour；
(14) 20 ~ 30mL dehydrated alcohol is added obtained by step (13) in reaction solution, stirring filters after precipitating is precipitated, and filter cake is with 15
~ 20mL deionized water and the washing of 5 ~ 10mL dehydrated alcohol filter 2 ~ 3 times；Gained filter cake is put into surface plate, is placed in 50 DEG C very
24 hours are dried in empty thermostatic drying chamber to get double esterification Gallic Acid base bagasse xylan benzoic ether.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110713559A (en) * | 2019-10-22 | 2020-01-21 | 桂林理工大学 | Method for synthesizing active cinnamic acid/p-chlorobenzoic acid bagasse xylan diester |
| CN110724212A (en) * | 2019-10-22 | 2020-01-24 | 桂林理工大学 | Synthetic method of anti-HIV (human immunodeficiency virus) active cinnamic acid/o-chlorobenzoic acid bagasse xylan diester |
| CN110724213A (en) * | 2019-10-22 | 2020-01-24 | 桂林理工大学 | Synthesis method of antiviral active bagasse xylan cinnamic acid/m-chlorobenzoic acid diester |
| CN110776583A (en) * | 2019-10-22 | 2020-02-11 | 桂林理工大学 | Method for synthesizing active bagasse xylan p-bromobenzoic acid/cinnamic acid diester |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106519079A (en) * | 2016-10-26 | 2017-03-22 | 桂林理工大学 | Synthetic method of anti-HIV-activity sulfonyl bagasse xylan polyethylene terephthalate |
| CN107586352A (en) * | 2017-10-01 | 2018-01-16 | 桂林理工大学 | A kind of preparation method with antitumor activity bagasse xylan gallic acid/ferulic acid ester |
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- 2018-10-21 CN CN201811225995.6A patent/CN109400736A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106519079A (en) * | 2016-10-26 | 2017-03-22 | 桂林理工大学 | Synthetic method of anti-HIV-activity sulfonyl bagasse xylan polyethylene terephthalate |
| CN107586352A (en) * | 2017-10-01 | 2018-01-16 | 桂林理工大学 | A kind of preparation method with antitumor activity bagasse xylan gallic acid/ferulic acid ester |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110713559A (en) * | 2019-10-22 | 2020-01-21 | 桂林理工大学 | Method for synthesizing active cinnamic acid/p-chlorobenzoic acid bagasse xylan diester |
| CN110724212A (en) * | 2019-10-22 | 2020-01-24 | 桂林理工大学 | Synthetic method of anti-HIV (human immunodeficiency virus) active cinnamic acid/o-chlorobenzoic acid bagasse xylan diester |
| CN110724213A (en) * | 2019-10-22 | 2020-01-24 | 桂林理工大学 | Synthesis method of antiviral active bagasse xylan cinnamic acid/m-chlorobenzoic acid diester |
| CN110776583A (en) * | 2019-10-22 | 2020-02-11 | 桂林理工大学 | Method for synthesizing active bagasse xylan p-bromobenzoic acid/cinnamic acid diester |
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Application publication date: 20190301 |